Windsor County Vacation Packages
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Your Windsor County Vacation
With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way.
Top vacation destinations in Windsor County
Top Windsor County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Deerfield Valley Inn
CA $1,389
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
9.4/10 Exceptional! (131 reviews)
We returned to this place on a quick 2-day/last minute get away. Owner is new from last time. Nice people; helpful and made a very good breakfast. Only issue we really had was the plumbing. Our room had some kind of venting issue with the sink/toilet/shower. Toilet bubbled and would go down at times; sink would go slow/stop at times; shower also stopped up and went down very slow. Told the owner about it and hopefully they can get it fixed. But overall, pleasant stay.
Reviewed on Aug 17, 2026
Emrose Luxury Cabins
CA $1,442
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
8.8/10 Excellent! (116 reviews)
The Cabins are very nice clean and cozy , love how well they were thought out to fit everything so perfectly in a small space . Full bathroom , full kitchen and nice size refrigerator and microwave .
Perfect for a romantic getaway . Plus the outdoor accommodations were great . And can’t wait for the soon to come restaurant and lounge for the guests . A++ stay .
Staff were very nice and helpful
Reviewed on Aug 26, 2026
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
CA $1,896
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9/10 Wonderful! (865 reviews)
There was a lot to love about Holiday Inn Club Vacations Mount Ascutney, especially for a larger family or group. Our three-bedroom villa was BY FAR the largest accommodation of our trip and surprisingly affordable. We had tons of room to spread out, a decent-sized kitchen for cooking, and FREE laundry—a huge win during a long road trip!
The villa kitchen was helpful but pretty minimally stocked. Cooking utensils and cutting boards were lacking, so bring some basics if you plan to cook. Grills are available, but you’ll need charcoal. I’d recommend buying it and any groceries before arriving because the onsite marketplace is expensive.
The biggest disappointment was the pool, which is closed through 2027. Traveling with kids, that was a major bummer and definitely something families should know before booking.
The location is incredibly beautiful, tucked away on a Vermont mountainside, but it is truly in the middle of nowhere. Come prepared!
Overall, the incredible amount of space and affordability made it work really well for our group. It wasn’t our favorite stay of the trip, but the value for a three-bedroom villa was hard to beat.
Reviewed on Aug 30, 2026
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
CA $1,831
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Rutland (RUT)
9.2/10 Wonderful! (67 reviews)
Nice area, clean and kitchen was well equipped. We used the air fryer for dinner one night.
Reviewed on Aug 15, 2026
Windsor County Hotel Deals
Align Inn Vermont
5817 Woodstock Rd Quechee VT
Fully refundableReserve now, pay when you stay
CA $184
CA $202 total
Sep 1 - Sep 2
includes taxes & fees
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
CA $569
CA $687 total
Sep 7 - Sep 8
includes taxes & fees
Hotel Coolidge
39 South Main Street White River Junction VT
Fully refundableReserve now, pay when you stay
CA $178
CA $195 total
Sep 6 - Sep 7
includes taxes & fees
8.2/10 Very good! (1,008 reviews)
"Very nice staff, but the property have large space to improve such as the windows, we have very noisy night,"
Reviewed on Aug 30, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Windsor County vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Windsor County from just CA $1,389. And the more you bundle, the more cash you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Windsor County?
You'll save a ton of money if you bundle your hotels, car rentals and flights into a Windsor County travel package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels all over the world, which means you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Windsor County?
Okemo Mountain Resort is one of the key things that lures people to Windsor County, so it makes perfect sense that many decide to book their hotel in Ludlow.
What are the top hotels in Windsor County?
When it comes to hotels in Ludlow, Super 8 by Wyndham White River Junction and Holiday Inn Express Hotel & Suites White River Junction, an IHG Hotel are two terrific options. If you're spending time in Plymouth, Hotel Coolidge and White River Inn and Suites will make you feel right at home.
How far in advance should I book my Windsor County vacation?
It depends on the airline, but you can usually browse through international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers will sometimes find a cheaper flight only weeks before their intended journey.
What does an Expedia Windsor County travel package include?
It comes down to what you're looking for. If you're traveling by yourself, you might decide to bundle hotels and flights. Bringing the entire family to Windsor County? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the freedom and flexibility to tailor your travel package.
What should I know before booking a Windsor County travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with great discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachside condos, chalets in the middle of mountains and even glamping tents!
Can I choose my airline with a Windsor County Expedia vacation package?
Most definitely. Expedia has more than 550 partner airlines to select from across the world. With so many choices, finding the ideal carrier to fly you to Windsor County will be a snap.
If I'm not able to travel, can I cancel my Windsor County vacation package?
We get it — unexpected stuff happens. If you've locked in a Windsor County vacation package and need to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But generally, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
Stay near popular Windsor County attractions
Okemo Mountain Resort
9.2/10 (510 reviews)
Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this romantic area.
Photo by Mike Gauthier
Quechee Gorge Bridge
9.2/10 (580 reviews)
Quechee Gorge Bridge is just one of the places to see in White River Junction, so why not enjoy the other things to explore during your travels? Wander the riverfront in this quaint area.
Photo by George Sykes
King Arthur Baking Company
9.4/10 (178 reviews)
You can enjoy retail therapy at King Arthur Baking Company during your stay in Norwich. While you're in the area, stroll along the riverfront.
Photo by Ed Gaffny
Quechee Gorge Village
9.0/10 (288 reviews)
You can enjoy retail therapy at Quechee Gorge Village during your trip to Quechee. Amble around the area's riverfront or seek out the ski slopes.
Billings Farm and Museum
9.2/10 (84 reviews)
You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.
Photo by William E Berry Jr.
Mount Ascutney
8.8/10 (27 reviews)
Commune with nature and explore the great outdoors at Mount Ascutney during your travels in Brownsville. You can seek out the ski slopes while in the area.
Simon Pearce Mill
9.0/10 (80 reviews)
Learn about the local history of Quechee when you spend time at Simon Pearce Mill. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
Upper Valley Aquatic Center
8.0/10 (43 reviews)
Enjoy a stop at Upper Valley Aquatic Center, an entertaining place to visit in White River Junction. Wander the riverfront in this quaint area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
